It's going to come down to your preference, but given the information provided, here's what you need to consider:
-Radio can be important only if you plan on using this as a portable radio, like if you're constantly on your feet and not using this in a home or car. you probably won't record the radio, its a feature I never used and I used to make mixed tapes off the radio all the time! (boy does that date me)
-Bluetooth is kinda the same thing. you think you need it, but probably won't use it.
-Additional memory is probably not that big of a deal either. If you're going 8Gb, you really won't get much more out of another card (especially for the money), so you probably won't use it.
Which really means its down to this:
-The Insignia probably uses .mp3 for and is compatible with .wma, so you'll be using Microsoft sound format, which I personally prefer, however I've been told by less technical people that it can be a little frustrating.
-The iPod uses iTunes, which has its set of ups and downs. iTunes has a lot of easily downloaded songs/movies, subscriptions to podcasts, and will consistently sync with your computer. The problem is that it isn't really drop in/drop out like folders in Mac or Windows because of the sync. It also means all tunes downloaded will be locked, ie: they won't work on anything but your personal iPod and the specific computer downloaded to. Also, iTunes converts all your music to a format that is only Mac, iTunes, or iPod compatible (and by default makes them "locked" as well). The iPod also has TONS of easy plug 'n play accessories.
If you're not confident about technology, probably the iPod. If you want a PC-based customizable player, go with the Insignia.
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